US6180064B1 - Semiconducting organic polymer gas sensor - Google Patents

Semiconducting organic polymer gas sensor Download PDF

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Publication number
US6180064B1
US6180064B1 US08/765,591 US76559197A US6180064B1 US 6180064 B1 US6180064 B1 US 6180064B1 US 76559197 A US76559197 A US 76559197A US 6180064 B1 US6180064 B1 US 6180064B1
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gas sensor
electrodes
recited
monomer
semiconducting
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Krishna C. Persaud
Paolo Pelosi
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AWD Pharma GmbH and Co KG
Genmark Diagnostics Inc
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Osmetech PLC
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Assigned to AROMASCAN, PLC reassignment AROMASCAN, PLC ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: PERSAUD, KRISHNA CHANDRA, PELOSI, PAOLO
Assigned to OSMETECH PLC reassignment OSMETECH PLC CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: AROMASCAN PLC
Assigned to OSMETECH PLC reassignment OSMETECH PLC CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: AROMASCAN PLC
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    • G—PHYSICS
    • G01—MEASURING; TESTING
    • G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N27/00—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means
    • G01N27/02—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance
    • G01N27/04—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance by investigating resistance
    • G01N27/12—Investigating or analysing materials by the use of electric, electrochemical, or magnetic means by investigating impedance by investigating resistance of a solid body in dependence upon absorption of a fluid; of a solid body in dependence upon reaction with a fluid, for detecting components in the fluid
    • G01N27/125—Composition of the body, e.g. the composition of its sensitive layer
    • G01N27/126—Composition of the body, e.g. the composition of its sensitive layer comprising organic polymers

Definitions

  • This invention relates to semiconducting organic polymers which may be used in gas sensors.
  • certain electrochemically prepared semiconducting polymers such as polypyrrole may be employed in sensors in order to detect gases, vapors and odors.
  • a sensor may comprise a pair of electrodes mounted on a substrate, with a layer of the semiconducting organic polymer deposited on and between the electrodes in order to produce an electrical connection between the electrodes.
  • the semiconducting organic polymer may be sensitive to the presence of a gas or, more likely, to a range of gases, to the extent that adsorption of the gas onto the polymer surface affects the electrical properties of the polymer.
  • the presence of gas may be detected by monitoring, for example, the change in DC resistance of the sensor on exposure to the gas.
  • a given semiconducting organic polymer will typically be sensitive to a range of compounds. Clearly this lack of selectivity is a major problem if one wishes to develop a sensor which is specific to a particular gas. Conversely, a sensor which employs a given semiconducting organic polymer may not be sufficiently sensitive to such a broad range of gases that it may be considered a general purpose device.
  • a solution to these problems is a device which employs a plurality of sensors, wherein each sensor incorporates a different polymer and each polymer possesses differing gas response profiles.
  • a suite of polymers may be selected which possess broadly overlapping responses, but which are individually chemically tailored to enhance differences in response to certain molecules or classes of molecules. Often the variation of a substituent group on the monomer unit is sufficient to enable such “fine tuning” of response.
  • a multi-sensor device detects gases and odors as a characteristic pattern of individual responses across the array of sensors.
  • the present invention relates to a class of semiconducting organic polymers based on 1, 2, 5 substituted five membered heterocyclic aromatic ring monomer units.
  • the substituent groups at the 2 and 5 positions are preferably aromatic rings; in particular, thienyl or thienyl derivatives appear to confer enhanced stability to the resulting polymer. Further substitution at the 3 position of the ring may be desirable.
  • U.S. Pat. No. 5,210,217 discloses a family of 3-substituted 2,5-di(2-thienyl)pyrrole polymers. These polymers are functionalised at the 3 position with an analyte specific receptor such as an enzyme and are employed in conductimetric liquid phase analyte detection.
  • a gas sensor which comprises:
  • one or more of the semiconducting organic polymers is polymerized from a monomer comprising a five membered heterocyclic aromatic ring with substituent groups at the 1, 2 and 5 positions.
  • the transduction means may comprise means for applying electric signal across the electrodes and detection means for detecting a chosen electrical property in the presence of a gas. For instance, if a DC electric signal is applied the change in polymer resistance on exposure of the sensor to a gas may be monitored; if an AC electric signal is applied, the change in an impedance characteristic, such as the capacitance, may be detected at a specific AC frequency.
  • the substituted five membered heterocyclic aromatic ring may be pyrrole.
  • the substituent groups at the 2 and 5 positions may be aromatic rings and, in particular, may be thienyl or derivatives thereof.
  • any of the polymers described above may be polymerised electrochemically from a solution containing the monomer and a counter-ion.
  • This counter-ion may be BF 4 ⁇ , PF 6 ⁇ , CLO 4 ⁇ , C 8 H 17 SO 3 ⁇ , Fe(CN) 6 3 ⁇ or CH 3 C 6 H 4 SO 3 ⁇ .
  • FIG. 1 shows a plan view of a silicon chip carrier
  • FIG. 2 shows the view from below a chip carrier
  • FIG. 3 shows the synthesis of N-substituted 2,5-Di-(2-thienyl)-pyrrole
  • FIG. 4 shows the electrochemical polymerization process
  • FIGS. 1 and 2 show an embodiment of a gas sensor based on a modified 40 pin silicon chip carrier 10 (Hybritek 40 L CC), wherein the gold pins 12 of the carrier are patterned onto a ceramic substrate 14 .
  • Adjacent pins 14 a and 16 a act as electrodes, and a layer of a semiconducting organic polymer 18 is deposited so that there is a semiconducting electrical connection between the electrodes 14 a and 16 a.
  • the electrodes are connected to plugs 14 b and 16 b , located on the underside of the chip carrier 10 .
  • the semiconducting organic polymer is polymerized from a monomer which comprises a five membered aromatic heterocyclic ring, the ring having at least two substituent groups wherein one substituent group is appended at the 2 position and another substituent group is appended at the 5 position.
  • Suitable heterocyclic rings are pyrrole, thiophene and furan.
  • heteroatom substituent group is not limited in scope and may be, for instance, alkyl, acyl or aryl.
  • a preferred choice as the five membered heterocyclic aromatic ring is pyrrole, and preferred substituents at the 2 and 5 positions are further aromatic rings.
  • the reason for the latter preference is that the polymerization of unsubstituted pyrrole proceeds almost exclusively via linkage at the 2 and 5 positions, and therefore it is possible to inhibit polymerization if the substituents at these positions do not themselves participate in the polymerization process.
  • the aromatic ring substituents may themselves be derivatized.
  • a class of monomer which has proved particularly useful is N-substituted 2,5-Di(2-thienyl)-pyrrole. Polymers based on this monomer unit have proved to be particularly stable when employed in gas sensors.
  • FIG. 3 The synthesis of 2,5-Di-(2-thienyl)-pyrrole and N-substituted derivatives thereof is shown in FIG. 3 .
  • 3-dimethylamino-1-(2-thienyl)-propanone hydrochloride (4) is produced in 89% yield by refluxing for 16 hours a mixture of 2-acetylthiophene (1), paraformaldehyde (2), dimethylamine hydrochloride (3) and concentrated hydrochloric acid in ethanol.
  • the product is isolated, treated with 35% aqueous ammonia and extracted with ether to yield 3-dimethylamino-1-(2-thienyl)-propanone (5).
  • the acid acts as a catalyst and the anhydride as a water scavenger which drives the equilibrium reaction towards the desired product.
  • An N-substituted derivative of 2,5-DTP (9) may be produced by using an appropriate primary amine instead of ammonium acetate.
  • the yield of (9) is often comparable to that of 2,5-DTP but does exhibit some dependence on the substituent group R; in particular, if R is bulky the yield may decrease substantially.
  • yields may be improved by the use of a benzene/acetic acid solvent system thus allowing the azeotropic removal of water from the reaction mixture by attaching a Dean-Stark trap.
  • a stronger acid catalyst such as titanium (IV) chloride can be used.
  • FIG. 4 shows the electrolytic oxidation of 2,5-Di-(2-thienyl)pyrrole in an electrochemical cell 40 .
  • the chip carrier 10 is connected, at plugs 14 b and 16 b , to the anode 42 of the cell 40 .
  • the cell 40 also comprises a cathode 44 , a standard calomel reference electrode 46 and is flushed with nitrogen through ports 48 .
  • the anode 42 is at 1.3 V with respect to the reference electrode 46 .
  • the electrolyte comprises 0.01 M 2,5-Di-(2-thienyl)pyrrole and 0.1 M tetraethylammonium p-toluenesulphonate in a 99% acetonitrile/1% water medium.
  • the further substituted variants are typically polymerized under similar conditions: the monomer concentration is typically between 0.01-0.1 M, and the solvent mixture is typically as described above, although a 50% dichloromethane, 49.5% acetonitrile, 0.5% water mixture is sometimes employed.
  • the tetraethylammonium p-toluenesulphonate yields the tosylate anion, which is incorporated into the polymer film during polymerization as a counter-ion to ensure overall electrical neutrality in the polymer.
  • Other counter-ions may be employed including, for example, BF 4 ⁇ , PF 6 ⁇ , ClO 4 ⁇ , C 8 H 17 SO 3 ⁇ or Fe(CN) 6 3 ⁇ .
  • Variation of the counter-ion is another means by which the response characteristics of a polymer may be moderated.

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  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Analytical Chemistry (AREA)
  • Electrochemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Biochemistry (AREA)
  • Immunology (AREA)
  • Pathology (AREA)
  • Investigating Or Analyzing Materials By The Use Of Fluid Adsorption Or Reactions (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Investigating Or Analyzing Materials By The Use Of Electric Means (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US08/765,591 1994-06-23 1995-06-20 Semiconducting organic polymer gas sensor Expired - Lifetime US6180064B1 (en)

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GB9412632A GB9412632D0 (en) 1994-06-23 1994-06-23 Semiconducting organic polymers
GB9412632 1994-06-23
PCT/GB1995/001450 WO1996000384A1 (en) 1994-06-23 1995-06-20 Semiconducting organic polymers

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US (1) US6180064B1 (de)
EP (1) EP0766819B1 (de)
JP (1) JP2931223B2 (de)
AT (1) ATE184397T1 (de)
AU (1) AU2745495A (de)
DE (1) DE69512065T2 (de)
DK (1) DK0766819T3 (de)
ES (1) ES2136862T3 (de)
GB (1) GB9412632D0 (de)
IL (1) IL114254A0 (de)
IN (1) IN182649B (de)
WO (1) WO1996000384A1 (de)

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7255677B2 (en) 2002-03-04 2007-08-14 Smiths Detection Inc. Detection, diagnosis, and monitoring of a medical condition or disease with artificial olfactometry
US20070281362A1 (en) * 2004-03-03 2007-12-06 Koninklijke Philips Electronics, N.V. Detection of No With a Semi-Conducting Compound and a Sensor and Device to Detect No
WO2014066704A1 (en) 2012-10-24 2014-05-01 Genmark Diagnostics, Inc. Integrated multiplex target analysis
US9222623B2 (en) 2013-03-15 2015-12-29 Genmark Diagnostics, Inc. Devices and methods for manipulating deformable fluid vessels
WO2016077364A2 (en) 2014-11-11 2016-05-19 Genmark Diagnostics, Inc. Instrument and cartridge for performing assays in a closed sample preparation and reaction system
WO2016077341A2 (en) 2014-11-11 2016-05-19 Genmark Diagnostics, Inc. Instrument and cartridge for performing assays in a closed sample preparation and reaction system employing electrowetting fluid manipulation
US9498778B2 (en) 2014-11-11 2016-11-22 Genmark Diagnostics, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US9598722B2 (en) 2014-11-11 2017-03-21 Genmark Diagnostics, Inc. Cartridge for performing assays in a closed sample preparation and reaction system
WO2018053501A1 (en) 2016-09-19 2018-03-22 Genmark Diagnostics, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US10106847B1 (en) 2017-08-24 2018-10-23 Clinical Micro Sensors, Inc. Electrochemical detection of bacterial and/or fungal infections
WO2019040769A1 (en) 2017-08-24 2019-02-28 Clinical Micro Sensors, Inc. (dba GenMark Diagnostics, Inc.) ELECTROCHEMICAL DETECTION OF BACTERIAL AND / OR FUNGAL INFECTIONS
US10495656B2 (en) 2012-10-24 2019-12-03 Genmark Diagnostics, Inc. Integrated multiplex target analysis
USD881409S1 (en) 2013-10-24 2020-04-14 Genmark Diagnostics, Inc. Biochip cartridge

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GB9713043D0 (en) * 1997-06-21 1997-08-27 Aromascan Plc Gas sensor
GB9717209D0 (en) * 1997-08-14 1997-10-22 Aromascan Plc Condition detector
GB9717306D0 (en) * 1997-08-15 1997-10-22 Aromascan Plc Method and device for detecting a condition
EP1076830A4 (de) * 1998-04-13 2001-10-24 Irdam Company Multifunktionssensor
US6575013B2 (en) * 2001-02-26 2003-06-10 Lucent Technologies Inc. Electronic odor sensor
US6494833B1 (en) 2001-06-19 2002-12-17 Welch Allyn, Inc. Conditioning apparatus for a chemical sensing instrument
FR2985314B1 (fr) * 2011-12-28 2015-01-16 Ct Scient Tech Batiment Cstb Developpement d'un microsysteme de detection

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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7255677B2 (en) 2002-03-04 2007-08-14 Smiths Detection Inc. Detection, diagnosis, and monitoring of a medical condition or disease with artificial olfactometry
US20070265509A1 (en) * 2002-03-04 2007-11-15 Smiths Detection Inc. Detection, diagnosis, and monitoring of a medical condition or disease with artificial olfactometry
US7819803B2 (en) 2002-03-04 2010-10-26 Smiths Detection Inc. Detection, diagnosis, and monitoring of a medical condition or disease with artificial olfactometry
US20070281362A1 (en) * 2004-03-03 2007-12-06 Koninklijke Philips Electronics, N.V. Detection of No With a Semi-Conducting Compound and a Sensor and Device to Detect No
WO2014066704A1 (en) 2012-10-24 2014-05-01 Genmark Diagnostics, Inc. Integrated multiplex target analysis
US9957553B2 (en) 2012-10-24 2018-05-01 Genmark Diagnostics, Inc. Integrated multiplex target analysis
EP2965817A1 (de) 2012-10-24 2016-01-13 Genmark Diagnostics Inc. Integrierte multiplex-zielanalyse
US11952618B2 (en) 2012-10-24 2024-04-09 Roche Molecular Systems, Inc. Integrated multiplex target analysis
EP3427830A1 (de) 2012-10-24 2019-01-16 Genmark Diagnostics Inc. Integrierte multiplex-zielanalyse
US10495656B2 (en) 2012-10-24 2019-12-03 Genmark Diagnostics, Inc. Integrated multiplex target analysis
USD900330S1 (en) 2012-10-24 2020-10-27 Genmark Diagnostics, Inc. Instrument
EP3919174A2 (de) 2012-10-24 2021-12-08 Genmark Diagnostics Inc. Integrierte multiplex-zielanalyse
US9453613B2 (en) 2013-03-15 2016-09-27 Genmark Diagnostics, Inc. Apparatus, devices, and methods for manipulating deformable fluid vessels
US10807090B2 (en) 2013-03-15 2020-10-20 Genmark Diagnostics, Inc. Apparatus, devices, and methods for manipulating deformable fluid vessels
US9222623B2 (en) 2013-03-15 2015-12-29 Genmark Diagnostics, Inc. Devices and methods for manipulating deformable fluid vessels
US9410663B2 (en) 2013-03-15 2016-08-09 Genmark Diagnostics, Inc. Apparatus and methods for manipulating deformable fluid vessels
US10391489B2 (en) 2013-03-15 2019-08-27 Genmark Diagnostics, Inc. Apparatus and methods for manipulating deformable fluid vessels
USD881409S1 (en) 2013-10-24 2020-04-14 Genmark Diagnostics, Inc. Biochip cartridge
WO2016077341A2 (en) 2014-11-11 2016-05-19 Genmark Diagnostics, Inc. Instrument and cartridge for performing assays in a closed sample preparation and reaction system employing electrowetting fluid manipulation
US9598722B2 (en) 2014-11-11 2017-03-21 Genmark Diagnostics, Inc. Cartridge for performing assays in a closed sample preparation and reaction system
WO2016077364A2 (en) 2014-11-11 2016-05-19 Genmark Diagnostics, Inc. Instrument and cartridge for performing assays in a closed sample preparation and reaction system
US9498778B2 (en) 2014-11-11 2016-11-22 Genmark Diagnostics, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US10005080B2 (en) 2014-11-11 2018-06-26 Genmark Diagnostics, Inc. Instrument and cartridge for performing assays in a closed sample preparation and reaction system employing electrowetting fluid manipulation
EP3831481A1 (de) 2014-11-11 2021-06-09 Genmark Diagnostics Inc. Instrument und kartusche zur durchführung von tests in einem geschlossenen probenvorbereitungs- und -reaktionssystem
US10864522B2 (en) 2014-11-11 2020-12-15 Genmark Diagnostics, Inc. Processing cartridge and method for detecting a pathogen in a sample
WO2018053501A1 (en) 2016-09-19 2018-03-22 Genmark Diagnostics, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US11300578B2 (en) 2016-09-19 2022-04-12 Roche Molecular Systems, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US12000847B2 (en) 2016-09-19 2024-06-04 Roche Molecular Systems, Inc. Instrument for processing cartridge for performing assays in a closed sample preparation and reaction system
US10273535B2 (en) 2017-08-24 2019-04-30 Clinical Micro Sensors, Inc. Electrochemical detection of bacterial and/or fungal infections
US11021759B2 (en) 2017-08-24 2021-06-01 Clinical Micro Sensors, Inc. Electrochemical detection of bacterial and/or fungal infections
US10669592B2 (en) 2017-08-24 2020-06-02 Clinical Micro Sensors, Inc. Electrochemical detection of bacterial and/or fungal infections
US10106847B1 (en) 2017-08-24 2018-10-23 Clinical Micro Sensors, Inc. Electrochemical detection of bacterial and/or fungal infections
WO2019040769A1 (en) 2017-08-24 2019-02-28 Clinical Micro Sensors, Inc. (dba GenMark Diagnostics, Inc.) ELECTROCHEMICAL DETECTION OF BACTERIAL AND / OR FUNGAL INFECTIONS

Also Published As

Publication number Publication date
AU2745495A (en) 1996-01-19
WO1996000384A1 (en) 1996-01-04
ES2136862T3 (es) 1999-12-01
DE69512065D1 (de) 1999-10-14
JP2931223B2 (ja) 1999-08-09
EP0766819A1 (de) 1997-04-09
JPH0815197A (ja) 1996-01-19
IN182649B (de) 1999-06-05
EP0766819B1 (de) 1999-09-08
DK0766819T3 (da) 2000-03-13
DE69512065T2 (de) 2000-02-24
GB9412632D0 (en) 1994-08-10
IL114254A0 (en) 1995-10-31
ATE184397T1 (de) 1999-09-15

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